All Of Anne Hathaway's Nippliest Fashion Moments, From 2002 To Now

Anne Hathaway was already one of fashion’s biggest vanguards long before her on-screen makeover in The Devil Wears Prada. And I’m not talking about her wearing merely chaotic Y2K trends like dresses over pants.

In the early aughts, few A-listers dared to bare breasts, lest they face public backlash. The rare brazen celebs who pulled off the look were Halle Berry and Sarah Jessica Parker, rocking scanty outfits on red carpets and at awards shows. Unlike those two, who were already Hollywood powerhouses at the time, Hathaway was an up-and-comer on the heels of The Princess Diaries. That didn’t keep her from embracing the highly controversial look.

For years, her risqué, nip-forward looks flew relatively under the radar. Shockingly, it wasn’t until 2013 — a year after filmmaker Lina Esco pioneered the #FreeTheNipple movement — that one of her “nipply” ensembles received major backlash, aka Dressgate. At the Oscars, Hathaway wore a pink dress constructed in a way that looked like she had pointy nipples. Even though it wasn’t actually sheer and nipples shouldn’t be contentious to begin with, the allusion to the body part riled people up, so much so that Hathaway felt the need to explain the snafu.

Little did Hathaway know that it would take another decade before the look would trend in Hollywood. Now, the likes of Kendall Jenner, Emily Ratajkowski, and Florence Pugh display breasts as frequently as they like. And they have the WeCrashed star to thank, in part.

Ahead, Hathaway’s most revealing ensembles that paved the way for bodily autonomy in Hollywood.

Anne’s Ruched LBD

Hathaway first freed the nip in 2002 at a special screening of the movie Chicago for a benefit. Inspired by the musical’s 1920s setting, she embodied the flapper attitude of flouting conventions and dress codes. The resulting look was a ruched dress with cinched details across the empire, waist, and hip, that was completely diaphanous.

She kept the look elegant with pointed pumps and a teeny white handbag.

Her Edgy Look

The following year, Hathaway attended the School of Rock premiere in a look heavily influenced by the film’s rock ‘n’ roll theme. Evocative of the early aughts, it included a ruffled and ruched minidress, studded knee-high boots, and crystal dangle earrings.

What wasn’t of the era, however, was how transparent the dress was. That was way ahead of its time.

A Sparkly LBD

She embraced the style again over a decade later. On the red carpet of The Intern’s New York premiere, her dramedy with Robert De Niro, she wore an asymmetrical LBD that was all sorts of riveting.

Covered in embroidery, it featured a one-sided shoulder with a lone long sleeve. Even the fringed hem featured an asymmetrical high-low cut, evocative of the 2010s. It also featured thin diagonal mesh panels along one breast that partly exposed nip.

Her Punk Dress

Fittingly, Hathaway’s most fashion-forward look of all time was at the “PUNK: Chaos to Couture”-themed Met Gala in 2013. In Valentino couture, she fully embodied the punk ethos. The ornate number was covered in beading that resembled a tiger’s stripes, and featured feather-trimmed long sleeves.

The gown’s punkiest feature was its see-through fabrication, which exposed everything she was wearing (or, rather, not wearing) underneath. Her bleached blond pixie was but a rock star bonus.

Honorable Mention: Her Infamous Oscars Dress

Her most notorious “nipple” dress, meanwhile, actually wasn’t all that nipply. In 2013, Hathaway attended the Oscars, where she took home the Best Supporting Actress award for her role in Les Misérables.

An angel in Prada, she looked every bit the winner, too. Her satin powder pink gown featured a sleeveless square neckline and an elegant column silhouette. It also featured darts that poked out, giving it a pointed nip effect.

Though this dress is the *least* revealing on this list, it received backlash. A year later, Hathaway explained the choice to wear the dress despite the conical detail, noting that she changed dresses at the last minute after realizing her initial gown would be too similar to Amanda Seyfried’s.

When she tried it on the morning of the Oscars, she already clocked the pointy darts. She told Harper’s Bazaar in an interview, “I look in the mirror, turn to [my husband] Adam, and say, ‘It looks like my nipples are hard.’ He says, ‘You look beautiful. Your nipples look pointy. The red carpet’s about to close. We gotta go.’”

Regardless of the reception, it was a style win in my book.